KR102169441B1 - An electroluminescent compound and an electroluminescent device comprising the same - Google Patents

Abstract

The present invention relates to an organic electroluminescent compound and an organic electroluminescent device including the same, wherein the organic electroluminescent compound according to the present invention has excellent thermal stability, high hole and electron transport capability, and power efficiency and driving voltage characteristics. It is excellent, and has the effect that the problem of concentration quenching due to steric hindrance and molecular association does not occur at all.

Description

An organic electroluminescent compound and an organic electroluminescent device comprising the same

The present invention relates to an organic electroluminescent compound and an organic electroluminescent device including the same.

Recently, organic light emitting devices capable of low voltage driving by self-luminous type have superior viewing angles and contrast ratios compared to liquid crystal displays (LCDs), which are the mainstream of flat panel display devices, and do not require a backlight, and are lightweight and thin. It is also advantageous in terms of power and is attracting attention as a next-generation display device due to its wide color reproduction range.

Organic light emitting diodes (OLEDs) are devices that emit light while electrons and holes form a pair and then disappear when charge is injected into an organic light emitting layer formed between an electron injection electrode (cathode) and a hole injection electrode (anode). to be.

An organic electroluminescent device using the organic light emitting phenomenon has a structure including an anode, a cathode, and an organic material layer therebetween. Here, the organic material layer is often made of a multilayer structure composed of different materials in order to increase the efficiency and stability of the organic electroluminescent device. For example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like. . In the structure of such an organic electroluminescent device, when a voltage is applied between the two electrodes, holes are injected from the anode and electrons from the cathode are injected into the organic material layer. It glows when it falls back to the ground.

The organic light emitting device can be formed on a flexible transparent substrate such as plastic, and can be driven at a voltage lower than 10 V compared to a plasma display panel or an inorganic light emitting display. It has the advantage of relatively low power consumption and excellent color. In addition, the organic electroluminescent device can display three colors of green, blue, and red, and thus has attracted much attention as a next-generation rich color display device.

In order for the organic electroluminescent device to fully exhibit the above-described excellent features, materials that form the organic material layer in the device, such as hole injection materials, hole transport materials, light-emitting materials, electron transport materials, and electron injection materials, are supported by stable and efficient materials. However, the development of a stable and efficient organic material layer material for an organic light emitting device has not been sufficiently developed. Therefore, in the related art, the development of new materials having low voltage driving, high efficiency and long life is continuously required.

In order to solve the above problems, the present invention has excellent thermal stability, high hole and electron transport capability, and excellent power efficiency and driving voltage characteristics, so that a pixel caused by a short circuit when an electric field is applied for a long time (eg, 100 hours or longer). It is intended to provide an organic electroluminescent compound that does not cause any defects.

In addition, there is no problem of crystallization at all, and uniformity of luminescence at high temperature can be secured, and solubility can be expressed more than 3% with respect to the solvent without the use of a separate thickener. It is intended to provide an organic electroluminescent compound capable of forming.

In addition, it is intended to provide an organic thin film layer for an organic electroluminescent device including the organic electroluminescent compound and an organic electroluminescent device including the same.

The present invention provides an organic electroluminescent compound of the following [Chemical Formula 1] or [Chemical Formula 2] in order to solve the above problems.

The definition of each substituent or skeleton atom will be described later.

[Formula 1]

[Formula 2]

In addition, the present invention provides an organic thin film layer for an organic electroluminescent device including at least one or more organic electroluminescent compounds represented by [Chemical Formula 1] or [Chemical Formula 2], and an organic electroluminescent device including the same.

The organic electroluminescent compound according to various embodiments of the present invention has excellent thermal stability, high hole and electron transport capabilities, as well as excellent power efficiency and driving voltage characteristics, so that it is short-circuited when an electric field is applied for a long time (eg, 100 hours or longer). It was confirmed that the problem of pixel defect caused by was not occurred at all.

In addition, the organic electroluminescent compound according to some embodiments of the present invention does not cause any problem of crystallization, and uniformity of light emission at high temperature can be secured, and the solubility 　 is 3 for solvents without using a separate thickener. % Or more could be expressed, and it was confirmed that film formation by a solution coating method was possible.

Hereinafter, the present invention will be described in more detail.

One aspect of the present invention relates to an organic electroluminescent compound represented by the following [Chemical Formula 1] or [Chemical Formula 2].

[Formula 1]

[Formula 2]

In the above [Formula 1] to [Formula 2],

R ₁ to R ₁₄ are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, and a substituted or unsubstituted C 3 to C 60 group. Heteroaryl group, substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, substituted or unsubstituted carbon number 6 to 30 arylamino group, substituted or unsubstituted C 1 to C 20 alkylsilyl group, substituted or unsubstituted C 6 to C 30 arylsilyl group, substituted or unsubstituted C 1 to C 50 arylalkylamino group, substituted Or an unsubstituted C2-C60 alkenyl group, a substituted or unsubstituted C2-C60 alkynyl group, a hydroxyl group, a nitro group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof , Phosphoric acid or a salt thereof, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms, a cyano group, a halogen group, selected from the group consisting of a small number and hydrogen, The R ₂ to R ₅ Among them, two adjacent Rs may be bonded to K to form a condensed ring.

Q is independently selected from the group consisting of CR ₁₅ R ₁₆ , NR ₁₇ , O, Se, P, S and SiR ₁₈ R ₁₉ , and Z is independently CR ₂₀ R ₂₁ , NR ₂₂ , O, S and SiR ₂₃ R _It is selected from the group consisting of ₂₄ .

Wherein R ₁₅ to R ₂₄ are hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms, a substituted or unsubstituted aryl group having 6 to 60 carbon atoms, a substituted or unsubstituted hetero aryl group having 3 to 60 carbon atoms, A substituted or unsubstituted alkoxy group having 1 to 60 carbon atoms, a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkylamino group having 1 to 20 carbon atoms, a substituted or unsubstituted C 6 to 30 carbon atom Arylamino group, substituted or unsubstituted alkylsilyl group having 1 to 20 carbon atoms, substituted or unsubstituted arylsilyl group having 6 to 30 carbon atoms, substituted or unsubstituted arylalkylamino group having 1 to 50 carbon atoms, substituted or unsubstituted Alkenyl group having 2 to 60 carbon atoms, substituted or unsubstituted alkynyl group having 2 to 60 carbon atoms, hydroxyl group, nitro group, amino group, amidino group, hydrazine, hydrazone, carboxyl group or salt thereof, sulfonic acid group or salt thereof, phosphoric acid Or a salt thereof, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, a substituted or unsubstituted arylthio group having 5 to 60 carbon atoms and a cyano group, and R ₁₅ to R ₂₄ And these substituents may be bonded to each other to form a condensed ring.

In addition, the R ₁₅ to R ₂₄ are each independently a hydrogen atom, a deuterium atom, a halogen atom, a hydroxyl group, a cyano group, a nitro group, an amidino group, a hydrazine, a hydrazone, a carboxyl group or a salt thereof, a sulfonic acid group or a salt thereof, phosphoric acid Or a salt thereof, an alkyl group having 1 to 60 carbon atoms, an alkenyl group having 2 to 60 carbon atoms, an alkynyl group having 2 to 60 carbon atoms, an alkoxy group having 1 to 60 carbon atoms, a cycloalkyl group having 3 to 60 carbon atoms, an aryl group having 6 to 60 carbon atoms , Aryloxy group having 6 to 60 carbon atoms, arylthio group having 6 to 60 carbon atoms, heteroaryl group having 2 to 60 carbon atoms, may be further substituted with one or more selected from -SiRRR and -NRR.

L is a single bond, a substituted or unsubstituted C1-C60 alkylene, a substituted or unsubstituted C2-C60 alkenylene, a substituted or unsubstituted C2-C60 alkynylene, a substituted or unsubstituted Cycloalkylene having 3 to 60 carbon atoms, heterocycloalkylene having 2 to 6 carbon atoms including one or more selected from N, O and S, substituted or unsubstituted arylene having 6 to 50 carbon atoms, and substituted or unsubstituted carbon number It is a divalent linking group selected from the group consisting of 3 to 50 heteroarylene, and m is an integer of 0 to 4.

X ₁ and X ₂ are CRR, and each R is independently hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 2 to 60 carbon atoms.

In (CR'R') _a of the [Formula 2], a is an integer of 3 to 6, and R'is each independently hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 60 carbon atoms Or a heteroaryl group having 2 to 60 carbon atoms.

In addition, with respect to Y, n is an integer of 0 to 1, and when n is 1, Y is CR"R", O or S, and R" is each independently hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, and 6 carbon atoms It is an aryl group of to 60 or a heteroaryl group of 2 to 60 carbon atoms.

According to an embodiment of the present invention, the compound according to [Formula 1] to [Formula 2] is one structure selected from the following [Formula A-1] to [Formula A-3] and the following [Formula B-1] To [Formula B-2] may be an organic electroluminescent compound having a structure in which the other structure selected from the bonded structure.

[Formula A-1]

[Formula A-2]

[Formula A-3]

[Formula B-1]

[Formula B-2]

In the [Chemical Formula A-1] to [Chemical Formula A-3], the bold portion and the bold portion in the [Chemical Formula B-1] to [Chemical Formula B-2] abut and have a bonded structure, and the Z 'Is selected from the group consisting of a single bond, CR ₃₁ R ₃₂ , NR ₃₃ , O, S, P, Se and SiR ₃₄ R ₃₅ , wherein Q, X ₁ , X ₁ , Y, R', n and a are It is the same as the definition in [Chemical Formula 1] to [Chemical Formula 2], and B is -(L) _m -R ₁ , and L, m and R ₁ are defined in [Chemical Formula 1] to [Formula 2] Is the same as

According to a preferred embodiment of the present invention, L may be any one selected from the following [Structural Formula C1] to [Structural Formula C14].

[Structural Formula C1] [Structural Formula C2] [Structural Formula C3] [Structural Formula C4]

[Structural Formula C5] [Structural Formula C6] [Structural Formula C7] [Structural Formula C8] [Structural Formula C9]

[Structural Formula C10] [Structural Formula C11] [Structural Formula C12] [Structural Formula C13] [Structural Formula C14]

In the [Structural Formula C1] to [Structural Formula C14],

Hydrogen or deuterium may be bonded to the carbon site of the ring in each structural formula, and R is the same as the definition of R ₁ to R ₁₄ in [Chemical Formula 1] or [Chemical Formula 2].

On the other hand, the aryl group contained in the organic light-emitting compound according to the present invention is an organic radical derived from an aromatic hydrocarbon by the removal of one hydrogen, and a single or fused ring system containing 5 to 7 members, preferably 5 or 6 members. In addition, when the aryl group has a substituent, it may be fused with neighboring substituents to further form a ring.

Specific examples of the aryl group include phenyl group, 2-methylphenyl group, 3-methylphenyl group, 4-methylphenyl group, 4-ethylphenyl group, o-biphenyl group, m-biphenyl group, p-biphenyl group, 4-methylbiphenyl group, 4 -Ethylbiphenyl group, o-terphenyl group, m-terphenyl group, p-terphenyl group, 1-naphthyl group, 2-naphthyl group, 1-methylnaphthyl group, 2-methylnaphthyl group, anthryl group, phenanthryl group, And aromatic groups such as pyrenyl group, indenyl, fluorenyl group, tetrahydronaphthyl group, pyrenyl, peryleneyl, chrysenyl, naphthacenyl, fluoranthenyl, and the like.

At least one hydrogen atom in the aryl group is a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a silyl group, an amino group (-NH ₂ , -NH(R), -N(R')(R"), R 'And R'are each independently an alkyl group having 1 to 10 carbon atoms, in this case referred to as an "alkylamino group"), an amidino group, a hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, an alkyl group having 1 to 24 carbon atoms, Halogenated alkyl group having 1 to 24 carbon atoms, alkenyl group having 1 to 24 carbon atoms, alkynyl group having 1 to 24 carbon atoms, heteroalkyl group having 1 to 24 carbon atoms, aryl group having 6 to 24 carbon atoms, arylalkyl group having 6 to 24 carbon atoms, carbon number It may be substituted with a 2 to 24 heteroaryl group or a C 2 to 24 heteroarylalkyl group.

Meanwhile, the heteroaryl group included in the organic light-emitting compound according to the present invention may be any one selected from the following [Structural Formula 1] to [Structural Formula 10].

[Structural Formula 1] [Structural Formula 2] [Structural Formula 3] [Structural Formula 4]

[Structural Formula 5] [Structural Formula 6] [Structural Formula 7]

[Structural Formula 8] [Structural Formula 9] [Structural Formula 10]

In the [Structural Formula 1] to [Structural Formula 10],

T ₁ to T ₁₂ are the same as or different from each other, and each independently, is selected from C (R ₄₁ ), C (R ₄₂ ) (R ₄₃ ), N, N (R ₄₄ ), O and S, and the R ₄₁ To R ₄₄ are the same as or different from each other, and each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted carbon number of 5 to It is selected from an aryl group of 30 and a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms having O, N, S or P as a hetero atom.

More preferably, the [Structural Formula 1] to [Structural Formula 10] may be any one selected from the following [Structural Formula 11].

[Structural Formula 11]

In [Structural Formula 11],

X is hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, a substituted or unsubstituted aryl group having 5 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or unsubstituted carbon number 2 to 20 alkynyl group, substituted or unsubstituted C 3 to C 30 cycloalkyl group, substituted or unsubstituted C 5 to C 30 cycloalkenyl group, substituted or unsubstituted C 1 to C 30 alkoxy group, substituted or unsubstituted A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms, a substituted or unsubstituted alkyl thioxy group having 1 to 30 carbon atoms, a substituted or unsubstituted arylthioxy group having 5 to 30 carbon atoms, a substituted or unsubstituted alkyl having 1 to 30 carbon atoms Selected from an amine group, a substituted or unsubstituted aryl group having 5 to carbon atoms, a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms having O, N, S or P as a hetero atom, a cyano group, a nitro group and a halogen group And m is an integer of 1 to 11, and when m is 2 or more, a plurality of Xs are the same or different from each other.

Specific examples of the alkyl group as a substituent used in the present invention include methyl group, ethyl group, propyl group, isopropyl group, isobutyl group, sec-butyl group, tert-butyl group, pentyl group, iso-amyl group, hexyl group, heptyl group , Octyl group, stearyl group, trichloromethyl group, trifluoromethyl group, etc., and at least one hydrogen atom of the alkyl group is a deuterium atom, a halogen atom, a hydroxy group, a nitro group, a cyano group, a trifluoromethyl group, a silyl group (In this case, referred to as "alkylsilyl group"), a substituted or unsubstituted amino group (-NH ₂ , -NH(R), -N(R')(R"), wherein R, R'and R" are each Independently, it is an alkyl group having 1 to 24 carbon atoms (referred to as an "alkylamino group" in this case), an amidino group, a hydrazine group, a hydrazone group, a carboxyl group, a sulfonic acid group, a phosphoric acid group, a C 1 to C 24 alkyl group, a C 1 to 24 C Halogenated alkyl group, C2-C24 alkenyl group, C2-C24 alkynyl group, C1-C24 heteroalkyl group, C5-C24 aryl group, C6-C24 arylalkyl group, C3-C24 hetero It may be substituted with an aryl group or a heteroarylalkyl group having 3 to 24 carbon atoms.

Specific examples of the alkoxy group as a substituent used in the present invention include a methoxy group, an ethoxy group, a propoxy group, an isobutyloxy group, a sec-butyloxy group, a pentyloxy group, an iso-amyloxy group, a hexyloxy group, and the like. May be substituted with the same substituent as in the case of the alkyl group.

Specific examples of the halogen group that is a substituent used in the compound of the present invention include fluorine (F), chlorine (Cl), bromine (Br), and the like.

The aryloxy group used in the present invention refers to an -O- aryl radical, wherein the aryl group is as defined above, and specific examples include phenoxy, naphthoxy, anthracenyloxy, phenanthrenyloxy, fluorenyl Oxy, indenyloxy, and the like, and one or more hydrogen atoms contained in the aryloxy group may be further substituted.

Specific examples of the silyl group as a substituent used in the present invention include trimethylsilyl, triethylsilyl, triphenylsilyl, trimethoxysilyl, dimethoxyphenylsilyl, diphenylmethylsilyl, diphenylvinylsilyl, methylcyclobutylsilyl, dimethyl Furylsilyl, etc. are mentioned.

Specific examples of the alkenyl group used in the present invention represent a linear or branched alkenyl group, 3-pentenyl group, 4-hexenyl group, 5-heptenyl group, 4-methyl-3-pentenyl group, 2,4 -Dimethyl-pentenyl group, 6-methyl-5-heptenyl group, 2,6-dimethyl-5-heptenyl group, etc. are mentioned.

The organic electroluminescent compound represented by [Chemical Formula 1] or [Chemical Formula 2] according to the present invention is not limited in its range in the following specific compounds, but more specifically, among compounds represented by [Chemical Formula 3] to [Chemical Formula 245] It may be selected.

The organic electroluminescent compound represented by [Chemical Formula 1] or [Chemical Formula 2] according to the present invention is not limited in its range in the following specific compounds, but more specifically, among compounds represented by [Chemical Formula 3] to [Chemical Formula 253] It may be selected.

[Formula 3] [Formula 4] [Formula 5] [Formula 6]

[Formula 7] [Formula 8] [Formula 9] [Formula 10]

[Formula 11] [Formula 12] [Formula 13] [Formula 14]

[Formula 15] [Formula 16] [Formula 17] [Formula 18]

[Formula 19] [Formula 20] [Formula 21] [Formula 22]

[Formula 23] [Formula 24] [Formula 25] [Formula 26]

[Formula 27] [Formula 28] [Formula 30] [Formula 31]

[Formula 32] [Formula 33] [Formula 34] [Formula 35]

[Formula 36] [Formula 37] [Formula 38] [Formula 39]

[Formula 40] [Formula 41] [Formula 42] [Formula 43]

[Formula 44] [Formula 45] [Formula 46] [Formula 47]

[Formula 48] [Formula 49] [Formula 50] [Formula 51]

[Formula 52] [Formula 53] [Formula 54] [Formula 55]

[Chemical Formula 56] [Chemical Formula 57] [Chemical Formula 58] [Chemical Formula 59]

[Formula 60] [Formula 61] [Formula 62] [Formula 63]

[Formula 64] [Formula 65] [Formula 66] [Formula 67]

[Formula 68] [Formula 69] [Formula 70] [Formula 71]

[Chemical Formula 72] [Chemical Formula 73] [Chemical Formula 74] [Chemical Formula 75]

[Chemical Formula 76] [Chemical Formula 77] [Chemical Formula 78] [Chemical Formula 79]

[Formula 80] [Formula 81] [Formula 82] [Formula 83]

[Formula 84] [Formula 85] [Formula 86] [Formula 87]

[Formula 88] [Formula 89] [Formula 90] [Formula 91]

[Formula 92] [Formula 93] [Formula 94] [Formula 95]

[Chemical Formula 96] [Chemical Formula 97] [Chemical Formula 98] [Chemical Formula 99]

[Formula 100] [Formula 101] [Formula 102] [Formula 103]

[Formula 104] [Formula 105] [Formula 106] [Formula 107]

[Formula 108] [Formula 109] [Formula 110] [Formula 111]

[Formula 112] [Formula 113] [Formula 114] [Formula 115]

[Chemical Formula 116] [Chemical Formula 117] [Chemical Formula 118] [Chemical Formula 119]

[Chemical Formula 120] [Chemical Formula 121] [Chemical Formula 122] [Chemical Formula 123]

[Formula 124] [Formula 125] [Formula 126] [Formula 127]

[Formula 128] [Formula 129] [Formula 130] [Formula 131]

[Formula 132] [Formula 133] [Formula 134] [Formula 135]

[Formula 136] [Formula 137] [Formula 138] [Formula 139]

[Formula 140] [Formula 141] [Formula 142] [Formula 143]

[Formula 144] [Formula 145] [Formula 146] [Formula 147]

[Formula 148] [Formula 149] [Formula 150] [Formula 151]

[Formula 152] [Formula 153] [Formula 154] [Formula 155]

[Formula 156] [Formula 157] [Formula 158] [Formula 159]

[Formula 160] [Formula 161] [Formula 162] [Formula 163]

[Formula 164] [Formula 165] [Formula 166] [Formula 167]

[Formula 168] [Formula 169] [Formula 170] [Formula 171]

[Formula 172] [Formula 173] [Formula 174] [Formula 175]

[Formula 176] [Formula 177] [Formula 178] [Formula 179]

[Formula 180] [Formula 181] [Formula 182] [Formula 183]

[Formula 184] [Formula 185] [Formula 186] [Formula 187]

[Formula 188] [Formula 189] [Formula 190] [Formula 191]

[Formula 192] [Formula 193] [Formula 194] [Formula 195]

[Chemical Formula 196] [Chemical Formula 197] [Chemical Formula 198] [Chemical Formula 199]

[Formula 200] [Formula 201] [Formula 202] [Formula 203]

[Formula 204] [Formula 205] [Formula 206] [Formula 207]

[Formula 208] [Formula 209] [Formula 210] [Formula 211]

[Chemical Formula 212] [Chemical Formula 213] [Chemical Formula 214] [Chemical Formula 215]

[Formula 216] [Formula 217] [Formula 218] [Formula 219]

[Formula 220] [Formula 221] [Formula 222] [Formula 223]

[Formula 224] [Formula 225] [Formula 226] [Formula 227]

[Formula 228] [Formula 229] [Formula 230] [Formula 231]

[Formula 232] [Formula 233] [Formula 234] [Formula 235]

[Formula 236] [Formula 237] [Formula 238] [Formula 239]

[Formula 240] [Formula 241] [Formula 242] [Formula 243]

[Formula 244] [Formula 245] [Formula 246] [Formula 247]

[Formula 248] [Formula 249] [Formula 250] [Formula 251]

[Chemical Formula 252] [Chemical Formula 253]

Another aspect of the present invention relates to an organic thin film layer for an organic electroluminescent device comprising at least one compound according to [Chemical Formula 1] to [Chemical Formula 2] according to various embodiments of the present invention.

According to an embodiment of the present invention, the organic thin film layer is characterized in that it further comprises at least one or more compounds represented by the following [Chemical Formula A-1] to [Chemical Formula J-1].

[General Formula A-1]

ML ₁ L ₂ L ₃

The M is selected from the group consisting of metals of groups 7, 8, 9, 10, 11, 13, 14, 15, and 16, preferably Ir, Pt, Pd, Rh, Re , Os, Tl, Pb, Bi, In, Sn, Sb, Te, Au and Ag. In addition, the L ₁ , L ₂ and L ₃ may be the same as or different from each other as a ligand, and may each independently include any one selected from the following [Structural Formula D], but is not limited thereto. In addition, * in the following [structural formula D] represents a site that binds to the metal ion M.

[Structural Formula D]

In the [Structural Formula D],

R is different from each other or the same, and each independently hydrogen, deuterium, halogen, cyano group, substituted or unsubstituted alkyl group having 1 to 30 carbon atoms, substituted or unsubstituted aryl group having 6 to 50 carbon atoms, substituted or unsubstituted A heteroaryl group having 5 to 50 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 30 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms, a substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms, a substituted or Unsubstituted C1-C30 alkylamino group, substituted or unsubstituted C1-C30 alkylsilyl group, substituted or unsubstituted C6-C30 arylamino group, and substituted or unsubstituted C6-C30 arylsilyl It may be any one selected from group.

Each of R is independently selected from an alkyl group having 1 to 20 carbon atoms, a cycloalkyl group having 3 to 20 carbon atoms, an aryl group having 6 to 40 carbon atoms, a heteroaryl group having 3 to 20 carbon atoms, a cyano group, a halogen group, deuterium and hydrogen It may be further substituted with one or more substituents.

In addition, the R may be connected to each of the adjacent substituents by alkylene or alkenylene to form an alicyclic ring and a monocyclic or polycyclic aromatic ring.

The L may be connected to an adjacent substituent with alkylene or alkenylene to form a spiro ring or a fused ring.

As a specific example, the dopant represented by [General Formula A-1] may be any one selected from the following compounds, but is not limited thereto.

[General Formula B-1]

In the above [general formula B-1],

M ^A1 represents the same metal ion as defined in [General Formula A-1], and Y ^A11 , Y ^A14 , Y ^A15 and Y ^A18 Each independently represents a carbon atom or a nitrogen atom, Y ^A12 , Y ^A13 , Y ^A16 and Y ^A17 each independently represent a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom, and a sulfur atom, L ^A11 , L ^A12 , L ^A13 , and L ^A14 each represent a linking group as defined above, and Q ^A11 and Q ^A12 represent a partial structure containing an atom bonded to M ^A1 .

An exemplary structure of the compound represented by [General Formula B-1] is as follows, but is not limited thereto.

[General Formula C-1]

In the above [general formula C-1],

M ^B1 represents the same metal ion as defined in [General Formula A-1], Y ^B11 , Y ^B14 , Y ^B15 and Y ^B18 each independently represent a carbon atom or a nitrogen atom, and Y ^B12 , Y ^B13 , Y ^B16 And Y ^B17 each independently represents a substituted or unsubstituted carbon atom, a substituted or unsubstituted nitrogen atom, an oxygen atom, and a sulfur atom, L ^B11 , L ^B12 , L ^B13 , L ^B14 represent a linking group, and Q ^B11 , Q ^B12 are It shows a partial structure containing an atom bonded to M ^B1 .

An exemplary structure of the compound represented by [General Formula C-1] is as follows, but is not limited thereto.

[General Formula D-1]

In the above [general formula D-1],

M ^C1 represents the same metal ion as defined in [General Formula A-1], and R ^C11 and R ^C12 are each independently a hydrogen atom, a substituent that connects to each other to form a 5-membered ring, and does not have any Represents a substituent, and R ^C13 and R ^C14 are each independently a hydrogen atom, a substituent that connects to each other to form a five-membered ring, and represents a substituent that does not have anything that connects to each other, and G ^C11 and G ^C12 are each independently a nitrogen atom, substituted Or an unsubstituted carbon atom, L ^C11 and L ^C12 represent a linking group, and Q ^C11 and Q ^C12 represent a partial structure containing an atom bonded to M ^C1 .

An exemplary structure of the compound represented by [General Formula D-1] is as follows, but is not limited thereto.

[General Formula E-1]

In the above [general formula E-1],

M ^D1 represents the same metal ion as defined in [General Formula A-1], G ^D11 and G ^D12 each independently represent a nitrogen atom, a substituted or unsubstituted carbon atom, and J ^D11 , J ^D12 , J ^D13 and Each of J ^D14 represents an atomic group required to form a five-membered ring independently, and L ^D11 and L ^D12 represent a linking group.

An exemplary structure of the compound represented by [General Formula E-1] is as follows, but is not limited thereto.

[General Formula F-1]

In the above [general formula F-1],

M ^E1 represents the same metal ion as defined in [General Formula A-1], and J ^E11 and J ^E12 each independently represent an atomic group required to form a 5-membered ring, and G ^E11 , G ^E12 , G ^E13 and G ^E14 each independently represents a nitrogen atom, a substituted or unsubstituted carbon atom, and Y ^E11 , Y ^E12 , Y ^E13 and Y ^E14 each independently represent a nitrogen atom, a substituted or unsubstituted carbon atom.

An exemplary structure of the compound represented by [General Formula F-1] is as follows, but is not limited thereto.

[General Formula G-1]

In the above [general formula G-1],

M ^F1 represents the same metal ion as defined in [General Formula A-1].

L ^F11 , L ^F12 and L ^F13 represent a linking group, R ^F11 , R ^F12 , R ^F13 and R ^F14 represent a substituent, and R ^F11 and R ^F12 , R ^F12 And R ^F13 , R ^F13 and R ^F14 may be linked to each other to form a ring, wherein the ring formed by R ^F1 and R ^F12 , R ^F13 and R ^F14 is a 5-membered ring. In addition, Q ^F11 and Q ^F12 represent a partial structure containing an atom bonded to M ^F1 .

An exemplary structure of the compound represented by [General Formula G-1] is as follows, but is not limited thereto.

[General Formula H-1] [General Formula H-2] [General Formula H-3]

In the above [General Formula H-1] to [General Formula H-3],

R ¹¹ , R ¹² are substituents of alkyl, aryl or heteroaryl; In addition, a fused ring may be formed with a substituent adjacent to each other, and q11 and q12 are integers of 0 to 4, preferably 0 to 2.

In addition, when q11 and q12 are 2 to 4, a plurality of R11 and R12 may be the same or different, respectively.

L ¹ is a ligand that binds to platinum, and is preferably a ligand capable of forming an ortho metalized platinum complex, a nitrogen-containing heterocyclic ligand, a diketone ligand, a halogen ligand, and more preferably an ortho metal. ) A ligand, a bipyridyl ligand or a phenanthroline ligand that forms a platinum complex.

n ¹ is an integer of 0 to 3, preferably 0, and m ¹ is 1 or 2, preferably 2.

In addition, it is preferable that n ¹ and m ¹ make the metal complex represented by the general formula H-1 become a neutral complex.

In the above [General Formula H-2],

R ²¹ , R ²² , n ² , m ² , q ²² , L ² are the same as R ¹¹ , R ¹² , n ¹ , m ¹ , q ¹² and L ¹ , respectively, and q ²¹ is an integer of 0 to 2 , 0 is preferred.

In the above [General Formula H-3],

R ³¹ , n ³ , m ³ , L ³ are the same as R ¹¹ , n ¹ , m ¹ , and L ¹ , respectively, and q ³¹ represents an integer of 0 to 8, preferably 0 to 2, and more than 0 desirable.

Examples of specific compounds of the [General Formula H-1] to [General Formula H-3] are as follows, but are not limited thereto.

[General Formula I-1]

In the above [general formula I-1],

Ring A, Ring B, Ring C, and Ring D represent a nitrogen-containing heterocycle in which any two rings of rings A to D may have a substituent, and the other two rings are an aryl ring or heterocycle that may have a substituent. Represents and represents an aryl ring, and a condensed ring can be formed by ring A and ring B, ring A and ring C, and/or ring B and ring D. X ¹ , X ² , X ³ and X ⁴ represent a nitrogen atom in which two of them are coordinated to a platinum atom, and the other two represent a carbon atom or a nitrogen atom. Q ¹ , Q ² and Q ³ each independently represent a divalent atom (term) or a bond, but Q ¹ , Q ² and Q ³ do not represent a bond at the same time. Z ¹ , Z ² , Z ³ and Z ⁴ are any two representing a coordination bond, and the other two represent a covalent bond, an oxygen atom or a sulfur atom.

Examples of specific compounds of the [General Formula I-1] are as follows, but are not limited thereto.

[General Formula J-1]

In the above [general formula J-1],

M represents the same metal ion as defined in [General Formula A-1], Ar1 represents a substituted or unsubstituted ring structure, and two azomethine bonds (-C=N-) bound to the M In this case, the nitrogen atom (N) is each bonded to the M, and as a whole, forms a tridentate ligand that is bonded to the M at three loci.

In addition, in Ar1, C represents a carbon atom constituting the ring structure represented by Ar1. In addition, R1 and R2 may be the same as or different from each other, and each represents a substituted or unsubstituted alkyl group or aryl group, and L represents a monodentate ligand.

In the above [general formula J-1], it is preferable that M is Pt. In addition, it is preferable that Ar1 is selected from a 5-membered ring, a 6-membered ring and a condensed ring group thereof.

Examples of specific compounds of the [General Formula J-1] are as follows, but are not limited thereto.

In addition, the organic thin film layer may further include various host compounds and various dopant compounds in addition to the organic electroluminescent compound and the dopant compound according to the present invention.

Another aspect of the present invention relates to an organic electroluminescent device comprising a first electrode, a second electrode, and at least one organic thin film layer interposed between the first electrode and the second electrode, wherein the organic thin film layer is the [Formula 1] ] To [Formula 2] to include an organic electroluminescent compound.

In addition, the organic thin film layer containing the organic light-emitting compound of the present invention further includes at least one selected from a hole injection layer, a hole transport layer, a functional layer having a hole injection function and a hole transport function at the same time, a light emitting layer, an electron transport layer, and an electron injection layer. can do.

In this case, the organic thin film layer interposed between the first electrode and the second electrode may include a light emitting layer, the light emitting layer is made of a host and a dopant, and the organic electroluminescent compound according to the present invention may be used as a host.

Meanwhile, a dopant material may be used together with a host for the emission layer. When the light emitting layer includes a host and a dopant, the content of the dopant may be generally selected from about 0.01 to about 20 parts by weight based on about 100 parts by weight of the host.

According to an embodiment of the present invention, at least one layer selected from the hole injection layer, the hole transport layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transport layer and the electron injection layer is formed by a monomolecular deposition method or a solution process. The organic light emitting device according to the present invention may be used in a display device, a display device, and a single color or white lighting device.

The organic electroluminescent device of the present invention may further include a known material for an organic electroluminescent device, if necessary. For example, a compound that transports holes having a bisarylamino structure or an N-arylcarbazolyl structure, or a compound that transports electrons having a benzoimidazolyl structure may be added. Specifically, a material for forming a hole injection or a hole transport layer, or an electron injection material to be described later may be used.

In the organic electroluminescent device of the present invention, at least one organic thin film layer including a light emitting layer is sandwiched between a cathode and an anode. In addition, at least one layer of the organic thin film layer contains the organic electroluminescent compound according to the present invention alone or as a component of a mixture.

The organic electroluminescent compound according to the present invention may be used in a hole injection layer, a hole transport layer, an electron injection layer, and an electron transport layer in addition to the emission layer. The organic electroluminescent device according to the present invention is an organic electroluminescent device in which an organic thin film layer is composed of a plurality of layers, specifically (anode/hole injection layer/light emitting layer/cathode), (anode/light emitting layer/electron injection layer/cathode), (anode /Hole injection layer/light-emitting layer/electron injection layer/cathode), (anode/hole injection layer/hole transport layer/light-emitting layer/electron injection layer/cathode), etc. are mentioned.

The organic electroluminescent device according to the present invention has a multi-layered structure of the organic thin film layer, thereby preventing a decrease in luminance or lifespan due to quenching. Further, if necessary, a light emitting material, a doping material, a hole injection material, or an electron injection material may be used in combination. In addition, the luminescence luminance and luminous efficiency may be improved by the doping material. In addition, the hole injection layer, the light emitting layer, and the electron injection layer may each be formed by a layer structure of two or more layers. In this case, in the case of the hole injection layer, a layer for injecting holes from the electrode is referred to as a hole injection layer, and a layer for receiving holes from the hole injection layer and transporting holes to the light emitting layer is referred to as a hole transport layer. Similarly, in the case of the electron injection layer, the layer injecting electrons from the electrode is referred to as an electron injection layer, and the layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer is referred to as an electron transport layer. Each of these layers is selected and used according to factors such as the energy level of the material, heat resistance, and adhesion to the organic layer or metal electrode.

As the hole injection material, a compound having the ability to transport holes, having a hole injection effect from the anode, an excellent hole injection effect with respect to the light emitting layer or the light emitting material, and excellent in thin film formation ability is preferable. Specifically, phthalocyanine derivatives, naphthalocyanine derivatives, porphyrin derivatives, benzidine triphenylamine, diamine triphenylamine, hexacyanohexaazatriphenylene, and derivatives thereof, and polyvinylcarbazole, polysilane, conductive polymer, etc. Polymer materials of, but are not limited to these.

Among the hole injection materials that can be used in the organic electroluminescent device of the present invention, a more effective hole injection material is a phthalocyanine derivative. Phthalocyanine (Pc) derivatives include, for example, H2Pc, CuPc, CoPc, NiPc, ZnPc, PdPc, FePc, MnPc, ClAlPc, ClGaPc, ClInPc, ClSnPc, Cl2SiPc, (HO)AlPc, (HO)GaPc, VOPc There are phthalocyanine derivatives and naphthalocyanine derivatives such as MoOPc and GaPc-O-GaPc, but are not limited thereto.

Further, carriers can also be increased or decreased by adding an electron-accepting material such as a TCNQ derivative to the hole injection material. A preferred hole transport material usable in the organic EL device of the present invention is an aromatic tertiary amine derivative. As an aromatic tertiary amine derivative, for example, N,N'-diphenyl-N,N'-dinaphthyl-1,1'-biphenyl-4,4'-diamine, N,N,N',N '-Tetrabiphenyl-1,1'-biphenyl-4,4'-diamine, or the like, or oligomers or polymers having these aromatic tertiary amine skeletons, but is not limited thereto.

As the electron injecting material, a compound having an ability to transport electrons, having an electron injecting effect from the cathode, an excellent electron injecting effect to a light emitting layer or a light emitting material, and excellent in thin film formation ability is preferable. In the organic EL device of the present invention, more effective electron injection materials are metal complex compounds and nitrogen-containing heterocyclic derivatives.

Examples of the metal complex compound include lithium 8-hydroxyquinolinate, bis(8-hydroxyquinolinate)zinc, tris(8-hydroxyquinolinate)aluminum, tris(8-hydroxyquinolinate) Nate) gallium, bis(10-hydroxybenzo[h]quinolinate)beryllium, bis(10-hydroxybenzo[h]quinolinate)zinc, etc. may be mentioned, but the present invention is not limited thereto.

Examples of the nitrogen-containing heterocyclic derivatives include oxazole, thiazole, oxadiazole, thiadiazole, triazole, pyridine, pyrimidine, triazine, phenanthroline, benzimidazole, imidazopyridine, and the like. Among them, benzimidazole derivatives, phenanthroline derivatives, and imidazopyridine derivatives are preferred.

As a preferred embodiment, these electron injection materials further contain a dopant, and in order to facilitate the reception of electrons from the cathode, a dopant represented by an alkali metal is more preferably doped near the cathode interface of the second organic layer. Examples of the dopant include an electron-donating metal, an electron-donating metal compound, and an electron-donating metal complex, and these reducing dopants may be used singly or in combination of two or more.

In the organic electroluminescent device of the present invention, in addition to at least one selected from organic electroluminescent compounds in the light emitting layer, at least one of a light emitting material, a doping material, a hole injection material, a hole transport material, and an electron injection material may be contained in the same layer. May be. In addition, in order to improve the stability of the organic electroluminescent device obtained by the present invention with respect to temperature, humidity, atmosphere, etc., a protective layer may be provided on the surface of the device, or the entire device may be protected by silicone oil or resin.

As the conductive material used for the anode of the organic electroluminescent device of the present invention, those having a work function greater than 4 eV are suitable, and carbon, aluminum, vanadium, iron, cobalt, nickel, tungsten, silver, gold, platinum, palladium, etc. And alloys thereof, metal oxides such as tin oxide and indium oxide used for ITO substrates and NESA substrates, and organic conductive resins such as polythiophene and polypyrrole are used. As the conductive material used for the negative electrode, those having a work function less than 4 eV are suitable, and magnesium, calcium, tin, lead, titanium, yttrium, lithium, ruthenium, manganese, aluminum, lithium fluoride, etc., and alloys thereof are used. , It is not limited to this. Examples of the alloy include magnesium/silver, magnesium/indium, lithium/aluminum, and the like, but are not limited thereto. The ratio of the alloy is controlled according to the temperature, atmosphere, and vacuum degree of the evaporation source, and is selected at an appropriate ratio. If necessary, the anode and the cathode may be formed by a layer structure of two or more layers.

In the organic electroluminescent device of the present invention, in order to emit light efficiently, it is preferable to make at least one surface sufficiently transparent in the emission wavelength region of the device. In addition, it is preferable that the substrate is also transparent. The transparent electrode is set such that a predetermined light transmittance is ensured by a method such as vapor deposition or sputtering using the above-described conductive material. It is preferable that the light transmittance of the electrode on the light-emitting surface is 10% or more. The substrate is not limited as long as it has mechanical and thermal strength and has transparency, but includes a glass substrate and a transparent resin film.

For the formation of each layer of the organic light emitting device of the present invention, any of dry film formation methods such as vacuum deposition, sputtering, plasma, and ion plating, or wet film formation methods such as spin coating, dipping, and flow coating may be applied. . The film thickness is not particularly limited, but needs to be set to an appropriate film thickness. When the film thickness is too thick, a large applied voltage is required to obtain a constant light output, resulting in poor efficiency. When the film thickness is too thin, pinholes or the like occur, and sufficient light emission luminance cannot be obtained even when an electric field is applied. A typical film thickness is preferably in the range of 5 nm to 10 µm, more preferably in the range of 10 nm to 0.2 µm.

In the case of the wet film formation method, the material for forming each layer is dissolved or dispersed in an appropriate solvent such as ethanol, chloroform, tetrahydrofuran, dioxane, or the like to form a thin film, but any solvent may be used. As a suitable solution for such a wet film formation method, a solution containing an organic electroluminescent material containing the aromatic amine derivative of the present invention and a solvent can be used as the organic electroluminescent material.

The organic electroluminescent device of the present invention can be used for flat light emitting devices such as flat panel displays of wall-mounted TVs, photocopiers, printers, light sources such as backlights or instruments of liquid crystal displays, display panels, signs, and the like. Further, the compound of the present invention can be used not only in organic electroluminescent devices, but also in fields such as electrophotographic photoreceptors, photoelectric conversion devices, solar cells, and image sensors.

In addition, if a person having ordinary knowledge in the technical field of the present invention is based on common sense at the time of filing and the disclosure of the present invention, the compound described in the claims of the present invention can be easily prepared without undue trial and error or advanced experimentation. It is self-evident that it will be available.

That is, although not all described in the following Examples, according to the experimental results of the present inventors, the size, orientation, possibility of steric hindrance, polarity difference, etc. of the substituents between the compounds described in the following Examples and the compounds not described in the following Examples can be seen Even if it appears that there may be a case, the specific manufacturing process described in the following examples is not very complicated and does not involve complex side reactions, so if you are a person skilled in the art of the present invention, the following based on common technical knowledge at the time of filing It is obvious that the compounds described in the claims of the present invention can be prepared without adding any special knowledge by only describing the specific manufacturing method of the examples.

Hereinafter, the present invention will be described in more detail by examples. However, the following examples are presented as examples, and the present invention is not limited thereto.

Synthesis example 1. Synthesis of Formula 3

Synthesis example 1-1. Synthesis of <1-a>

<1-a> was synthesized according to the following Scheme 1.

[Scheme 1]

<1-a>

Phenylhydrazine 40g (0.3699mol), 2-methylcyclohexanone 41.5g (0.3699mol), and 240 mL of acetic acid were added to a 500 mL round-bottom flask and refluxed for 6 hours. After the reaction was completed, the reaction solution was basified with sodium hydroxide. After neutralization by extraction with water and ethylene acetate, the organic layer was anhydrous treated with magnesium sulfate, concentrated under reduced pressure, and 57.5g of <1-a> obtained by separating by column chromatography using hexane and methylene chloride as developing solvents (yield 84 %) obtained.

Synthesis example 1-2. Synthesis of <1-b>

<1-b> was synthesized according to Scheme 2 below.

[Scheme 2]

<1-b>

Dissolve <1-a> 50g (0.2699mol) obtained from Formula 1 in 150 mL of toluene in a 500 mL round-bottom flask in a nitrogen atmosphere, and then lower the temperature to -20 degrees below zero. 260 mL (0.1753 mol) of 1.6M methyllithium was slowly added dropwise to the above solution and reacted at -20 degrees Celsius for 3 hours. After the reaction was completed, 200 mL of a 1:1 solution of toluene and water was slowly poured into the reaction solution. The layers were separated, the organic layer was anhydrous treated with magnesium sulfate, concentrated under reduced pressure, and separated by hexane and column chromatography to obtain 47.3 g (yield 87%) of <1-b>.

Synthesis example 1-3. Synthesis of <1-c>

<1-c> was synthesized according to Scheme 3 below.

[Scheme 3]

<1-c>

<1-b> 44.5g (0.221mol), iodobenzene 67.6g (0.332mol), tris(dibenzylideneacetone)dipalladium (Pd ₂ (dba) ₃ ) synthesized in Scheme 2 in a 1L round bottom flask 4.0g (0.004mol), sodium tertiary butoxide (Na-t-BuO) 42.5g (0.442mol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl 2.7g ( 0.004 mol) and 445 mL of toluene were added and refluxed for 12 hours. After completion of the reaction, the reaction solution was cooled to room temperature, concentrated under reduced pressure, and then <1-c> 52.0g (yield 84.8%) was obtained by column chromatography.

Synthesis example 1-4. Synthesis of <1-d>

<1-d> was synthesized according to Scheme 4 below.

[Scheme 4]

<1-d>

In a 1L round bottom flask in a nitrogen atmosphere, 50.2g (0.181mol) of <1-d> synthesized in Scheme 3 and 500 mL of dimethylformamide were added, and the temperature inside the reactor was cooled to 0℃. When the temperature reaches 0℃, 35.4g (0.199mol) of N-bromosuccinimide is dissolved in 250 mL of dimethylformamide and then slowly added dropwise. After dropwise addition, the temperature is raised to room temperature and stirred. When the reaction was completed, the layers were separated with ethyl acetate and water, and the organic layer was dried under reduced pressure, and then <1-d> 58.4g (yield 90.6%) was obtained by column chromatography.

Synthesis example 1-5. Synthesis of <1-e>

<1-e> was synthesized according to Scheme 5 below.

[Scheme 5]

<1-e>

In a 1L round-bottom flask, <1-d> 35.0 g (0.098 mol) synthesized in Scheme 4, bis(pinacolato)diboron 37.4 g (0.147 mol), PdCl ₂ (dppf) 1.6 g (0.002 mol), potassium After adding 28.90 g (0.295 mol) of acetate, 525 mL of toluene was added and refluxed at 110°C for 12 hours. When the reaction is finished, it is filtered under reduced pressure while hot. The solution was dried under reduced pressure, and then <1-e> 27.7 g (yield 69.9%) was obtained by column chromatography.

Synthesis example 1-6. Synthesis of <1-f>

<1-f> was synthesized according to Scheme 6 below.

[Scheme 6]

<1-f>

In a 500 mL round-bottom flask, <1-e> 26.4 g (0.065 mol) obtained from Scheme 5, 2-bromonitrobenzene 11.0 g (0.054 mol), tetrakistriphenylphosphine palladium (Pd(PPh ₃ ) ₄ ) ) 3.1 g (0.003 mol), potassium carbonate (K ₂ CO ₃ ) 22.6 g (0.163 mol), water 55.0 mL, toluene 110.0 mL, and ethanol 55.0 mL were added and refluxed for 24 hours. When the reaction was completed, the reaction product was separated into layers to remove an aqueous layer, and the organic layer was separated and concentrated under reduced pressure, and <1-j> 13.0g (yield 59.9%) was obtained through column chromatography.

Synthesis example 1-7. Synthesis of <1-g>

<1-g> was synthesized according to Scheme 7 below.

[Scheme 7]

<1-g>

In a 250 mL round bottom flask, <1-f> 13.0 g (0.0326 mol) synthesized in Scheme 6, triphenylphosphine (PPH ₃ ) 25.6 g (0.0978 mol) and 1,2-dichlorobenzene 70 mL were added. Refluxed for time. When the reaction was completed, after cooling to room temperature, crystals were precipitated with 300 mL of methanol, filtered, and the filtered solid was filtered to obtain <1-g> 9g (yield 80%).

Synthesis example 1-8. Synthesis of <1-h>

<1-h> was synthesized according to Scheme 8 below.

[Scheme 8]

<1-h>

After creating a nitrogen atmosphere in a 100 mL reactor, 3.36 g (0.1384 mol) of magnesium, 40 mL of dry tetrahydrofuran, and a small amount of iodine were added and stirred for 30 minutes. To this mixed pressure solution, 20 mL of a dry tetrahydrofuran solution of 19.2 g (0.1216 mol) of bromobenzene was added dropwise at Yeongdo. After the dropwise addition, the mixture was heated and stirred at 65 °C for 2 hours. Dissolve 18 g (0.0568 mol) of 2-diphenylamino-4,6-dichloro-1,3,5-triazine in 100 mL of dry tetrahydrofuran in a 250 mL reactor, and then add the mixture of 100 mL reactor dropwise at Yeongdo. . After dropwise addition, the mixture is stirred at room temperature for 12 hours. When the reaction is complete, add 200 mL of 2N HCl, add ethyl acetate and water, and extract. The organic layer was subjected to anhydrous treatment, concentrated under reduced pressure, and then <1-h> 9.8g (yield 64.5%) was obtained by column chromatography.

Synthesis example 1-9. Synthesis of [Formula 3]

[Chemical Formula 3] was synthesized by the following Scheme 10.

[Scheme 9]

[Formula 3]

In a 500 mL round bottom flask, sodium hydride (60% mineral oil) (NaH), 0.8 g (0.020 mol), and 50.0 mL of N,N-dimethylformamide were added in a nitrogen atmosphere, and the reaction solution was cooled to 0 °C. A solution of <1-g> 5.0 g (0.014 mol) synthesized in [Scheme 7] at 0° C. dissolved in 50.0 mL of N,N-dimethylformamide is slowly added dropwise, and after the dropwise addition, the solution is maintained at 0° C. and stirred for 1 hour. . After 1 hour, a solution of <1-h> 4.4 g (0.016 mol) synthesized in [Scheme 8] dissolved in 150 mL of N,N-dimethylformamide is slowly added dropwise. When the dropwise addition is complete, the reaction solution is raised to room temperature and stirred. When the reaction is complete, the reaction solution is poured into 1 L of water to precipitate a solid and then filtered. The solid was recrystallized using toluene to obtain 4.7 g (yield 57.6%) of [Chemical Formula 3].

MS(MALDI-TOF): m/z 597.29[M] ⁺

Anal. Calc. for C ₄₁ H ₃₅ N ₅ C, 82.38; H, 5.90; N, 11.72. Found C, 82.36; H, 5.91; N, 11.73

Synthesis example 2. Synthesis of [Formula 5]

Synthesis example Synthesis of 2-1 and <2-a>

<2-a> was synthesized according to Scheme 10 below.

[Scheme 10]

<2-a>

To a 10 L round bottom flask, 500.0 g (2.702 mol) of 3-bromoaldehyde, 251.7 g (2.702 mol) of aniline, and 5000 mL of toluene were added and refluxed for 12 hours. When the reaction was completed, the reaction solution was cooled to room temperature, concentrated under reduced pressure, and dried under reduced pressure to obtain 701.0 g (yield 99.9%).

Synthesis example 2-2. Synthesis of <2-b>

<2-b> was synthesized according to Scheme 11 below.

[Scheme 11]

<2-b>

In a 5 L round-bottom flask, <2-a> 415.0 g (1.595 mol) synthesized in Scheme 10, benzamide hydrochloride 499.7 g (3.191 mol), sodium hydroxide 134.0 g (3.350 mol), and ethanol 3320 mL were added. After refluxing for 16 hours, 76.6 g (0.798 mol) of sodium tertiary butoxide was added and refluxed. When the reaction was completed, the reaction solution was cooled to room temperature, 1.5 L of water was added, and then filtered. The solid was stirred in 3 L of a 1:1 mixture of water and acetone and then filtered to obtain 300.0 g (yield 48%) of <2-b>.

Synthesis example 2-3 Synthesis of [Formula 5]

[Chemical Formula 5] was synthesized by the following Scheme 12.

[Scheme 12]

[Formula 5]

In a 250 mL round-bottom flask, <1-g> 5.0 g (0.014 mol) synthesized in Scheme 7, <2-b> 6.9 g (0.018 mol) synthesized in Scheme 11, tris(dibenzylideneacetone)dipalladium (Pd2(dba)3) 0.2 g (0.000 mol), sodium tertiary butoxide (Na-t-BuO) 2.6 g (0.0.27 mol), and toluene 445 mL were added, and the temperature was raised to 60° C. 0.40g (0.001mol) tertiary butylphosphine was added and refluxed for 12 hours. Upon completion of the reaction, the reaction solution was poured into 300 mL of methanol to precipitate crystals and filtered. The filtered solid was subjected to column chromatography to obtain 5.8 g (yield 63.1%) of [Chemical Formula 5].

MS(MALDI-TOF): m/z 673.32[M] ⁺

Anal. Calc. for C ₄₇ H ₃₉ N ₅ C, 83.77; H, 5.83; N, 10.39. Found C, 83.78; H, 5.84; N, 10.37

Synthesis example 3. Synthesis of [Formula 34]

Synthesis example 3-1. Synthesis of <3-a>

<3-a> was synthesized according to Scheme 13 below.

[Scheme 13]

<3-a>

In a 500 mL round-bottom flask, <1-d> 21.5g (0.06mol) synthesized in Scheme 4, methyl anthranirate 10.9g (0.072mol), palladium diacetate 0.27g (0.001mol), xantphos 1.26g ( 0.002 mol), 27.5 g (0.084 mol) of cesium carbonate, and 215 mL of toluene were added and refluxed for 12 hours. When the reaction was completed, the reaction solution was concentrated under reduced pressure and then <3-a> 14.8g (yield 57.5%) was obtained using column chromatography.

Synthesis example 3-2. Synthesis of <3-b>

<3-b> was synthesized according to Scheme 14 below.

[Scheme 14]

<3-b>

In a 500 mL round-bottom flask under a nitrogen atmosphere, 14.8 g (0.035 mol) of <3-a> synthesized in Scheme 13 and 220 mL of isopropyl ether were added and cooled to 0°C. At 0℃, 40.5 mL (0.121 mol) of methylmagnesium bromide is slowly added dropwise. After dropwise addition, it is stirred at room temperature. When the reaction is complete, an aqueous ammonium chloride solution is slowly added dropwise, followed by layer separation with ethyl acetate and water. The organic layer was concentrated under reduced pressure and dried under reduced pressure to give 15.7 g (yield 99.5%) of <3-b>.

Synthesis example 3-3. Synthesis of <3-c>

<3-c> was synthesized according to Scheme 15 below.

[Scheme 15]

<3-c>

Into a 300 mL round-bottom flask, <3-b> 15.7g (0.035mol) synthesized in Scheme 14 and 157 mL of phosphoric acid were added and stirred at 50° C. for 24 hours. When the reaction was completed, the resulting solid was filtered, the solid was stirred in 500 mL of water, filtered, and the solid was dissolved in toluene and recrystallized with methanol to give <3-c> 6g (yield 42.5%).

Synthesis example 3-3. Synthesis of [Formula 34]

[Chemical Formula 34] was synthesized by the following Scheme 16.

[Scheme 16]

[Formula 34]

Except for using <3-c> synthesized in Scheme 15 instead of <1-g> used in Scheme 9, [Chemical Formula 34] 5g (yield 52.3%) was obtained.

MS(MALDI-TOF): m/z 639.34[M] ⁺

Anal. Calc. for C ₄₄ H ₄₁ N ₅ C,82.60; H, 6.46; N, 10.95. Found C, 82.61; H, 6.44; N, 10.96

Synthesis example 4. Synthesis of [Formula 36]

Synthesis example 4-1. Synthesis of [Formula 35]

[Chemical Formula 26] was synthesized by the following Scheme 17.

[Scheme 17]

[Formula 36]

[Chemical Formula 36] 4.8g (yield 58.3%) was obtained by synthesizing in the same manner except for using <3-c> synthesized in Scheme 15 instead of <1-g> used in Scheme 12.

MS(MALDI-TOF): m/z 715.37[M] ⁺

Anal. Calc. for C ₅₀ H ₄₅ N ₅ C,83.88; H, 6.34; N, 9.78. Found C, 83.85; H, 6.36; N, 9.79

Synthesis example 5. Synthesis of [Formula 44]

Synthesis example 5-1. Synthesis of <5-a>

<5-a> was synthesized according to Scheme 18 below.

[Scheme 18]

<5-a>

Except that phenyl magnesium bromide was used instead of methyl magnesium bromide used in Scheme 14, it was synthesized in the same manner to obtain 8.7 g (yield 98.7%) of <5-a>.

Synthesis Example 5-2. Synthesis of <5-b>

<5-b> was synthesized according to Scheme 19 below.

[Scheme 19]

<5-b>

<5-b> 7g (yield 86.0%) was obtained by synthesizing in the same manner except for using <5-a> synthesized in Scheme 18 instead of <3-b> used in Scheme 15.

Synthesis example 5-3. Synthesis of [Formula 44]

[Chemical Formula 44] was synthesized by the following Scheme 20.

[Scheme 20]

[Formula 44]

Except for using <5-b> synthesized in Scheme 19 instead of <1-g> used in Scheme 9, [Formula 34] 5g (yield 52.3%) was obtained.

MS(MALDI-TOF): m/z 763.37[M] ⁺

Anal. Calc. for C ₅₄ H ₄₅ N ₅ C, 84.90; H, 5.94; N, 9.16. Found C, 84.90; H, 5.94; N, 9.16

Synthesis example 6. Synthesis of [Formula 46]

Synthesis example 6-1. Synthesis of [Formula 46]

[Chemical Formula 46] was synthesized by the following Scheme 21.

[Scheme 21]

[Chemical Formula 46]

[Chemical Formula 46] 4.8g (yield 56.2%) was obtained by synthesizing in the same manner except for using <5-b> synthesized in Scheme 19 instead of <1-g> used in Scheme 12.

MS(MALDI-TOF): m/z 763.37[M] ⁺

Anal. Calc. for C ₅₄ H ₄₅ N ₅ C,84.90; H, 5.93; N, 9.17. Found C, 84.95; H, 5.90; N, 9.15

Synthesis example 7. Synthesis of [Formula 84]

Synthesis example 7-1. Synthesis of <7-a>

<7-a> was synthesized according to Scheme 22 below.

[Scheme 22]

<7-a>

In a 1000 mL round-bottom flask, 25 g (0.128 mol) of 4-bromoindole and 500 mL of acetic acid were added and stirred, and the temperature of the reaction mixture was cooled to 0 °C. Sodium cyanoborohydride 24.5g (0.390mol) was slowly added three times. After adding, it was stirred at room temperature. When the reaction was completed, the resultant of the reaction was poured into water, stirred, basified with sodium hydroxide, extracted, the organic layer was concentrated under reduced pressure, and then <4-a> 17.2g (yield 51.9%) was obtained by column chromatography.

Synthesis example 7-2. Synthesis of <7-b>

<7-b> was synthesized according to Scheme 23 below.

[Scheme 23]

<7-b>

<1-b> used in Scheme 3 was synthesized in the same manner except that <7-a> synthesized in Scheme 22 was used, and <7-b> 24g (yield 76.4%) was obtained.

Synthesis example 7-3. Synthesis of <7-c>

<7-c> was synthesized according to Scheme 24 below.

[Scheme 24]

<7-c>

<1-b> used in Scheme 5 was synthesized in the same manner, except that <7-b> synthesized in Scheme 23 was used, and <7-c> 14g (62% yield) was obtained.

Synthesis example 7-4. Synthesis of <7-d>

<7-d> was synthesized according to Scheme 25 below.

[Scheme 25]

<7-d>

Except for using <7-e> synthesized in Scheme 24 instead of <1-e> used in Scheme 6, <7-d> 11.8g (yield 69.1%) was obtained.

Synthesis example 7-5. Synthesis of <7-e>

<7-e> was synthesized according to Scheme 26 below.

[Scheme 26]

<7-e>

<1-f> used in Scheme 7 was synthesized in the same manner except that <7-d> synthesized in Scheme 25 was used, and <7-e> 8g (yield 75.4%) was obtained.

Synthesis example 7-6. Synthesis of [Formula 84]

[Chemical Formula 84] was synthesized by the following Scheme 27.

[Scheme 27]

[Formula 84]

[Chemical Formula 84] 4.9g (yield 52.3%) was obtained by synthesizing in the same manner except for using <7-e> synthesized in Scheme 26 instead of <1-g> used in Scheme 9.

MS(MALDI-TOF): m/z 515.21[M] ⁺

Anal. Calc. for C ₃₅ H ₂₅ N ₅ C, 81.53; H, 4.89; N, 13.58. Found C, 81.50; H, 4.90; N, 13.60

Synthesis example 8. Synthesis of [Formula 86]

Synthesis example 8-1. Synthesis of [Formula 86]

[Chemical Formula 86] was synthesized by the following Scheme 28.

[Scheme 28]

[Formula 86]

[Chemical Formula 46] 4.8g (yield 56.2%) was obtained by synthesizing in the same manner except for using <7-e> synthesized in Scheme 26 instead of <1-g> used in Scheme 12.

MS(MALDI-TOF): m/z 591.24[M] ⁺

Anal. Calc. for C ₄₁ H ₂₉ N ₅ C,83.22; H, 4.94; N, 11.84. Found C, 83.22; H, 4.94; N, 11.84

Synthesis example 9. Synthesis of [Formula 172]

Synthesis example 9-1. Synthesis of <9-a>

<9-a> was synthesized according to Scheme 29 below.

[Scheme 29]

<9-a>

Except for using 1,2,3,4-tetrahydroquinoline instead of <1-b> used in Scheme 3, it was synthesized in the same manner to obtain <9-a> 18.6g (yield 82.4%).

Synthesis example 9-2. Synthesis of <9-b>

<9-b> was synthesized according to Reaction Scheme 30 below.

[Scheme 30]

<9-b>

Except for using <9-a> synthesized in Scheme 29 instead of <1-d> used in Scheme 4, <9-b> 21g (yield 89.9%) was obtained.

Synthesis example 9-3. Synthesis of <9-c>

<9-c> was synthesized according to Scheme 31 below.

[Scheme 31]

<9-c>

<1-b> used in Scheme 5 was synthesized in the same manner, except that <9-b> synthesized in Scheme 30 was used, and 15g (yield 62%) was obtained.

Synthesis example 9-4. Synthesis of <9-d>

<9-d> was synthesized according to Scheme 32 below.

[Scheme 32]

<9-d>

<1-e> used in Scheme 6 was synthesized in the same manner, except that <9-c> synthesized in Scheme 31 was used, and <9-d> 10.8g (yield 61.1%) was obtained.

Synthesis example 9-5. Synthesis of <9-e>

<9-e> was synthesized according to Reaction Scheme 33 below.

[Scheme 33]

<9-e>

<1-f> used in Scheme 7 was synthesized in the same manner except that <9-d> synthesized in Scheme 32 was used, and <9-e> 10g (yield 54.4%) was obtained.

Synthesis example 9-6. Synthesis of [Formula 172]

[Chemical Formula 172] was synthesized by the following Scheme 34.

[Scheme 34]

[Chemical Formula 172]

[Chemical Formula 172] 5.0g (yield 54.3%) was obtained by synthesizing in the same manner except that <9-e> synthesized in Scheme 33 was used instead of <1-g> used in Scheme 9.

MS(MALDI-TOF): m/z 529.23[M] ⁺

Anal. Calc. for C ₃₆ H ₂₇ N ₅ C, 81.64; H, 5.14; N, 13.22. Found C, 81.66; H, 5.15; N, 13.21

Synthesis example 10. Synthesis of [Formula 174]

Synthesis example 10-1. Synthesis of [Formula 174]

[Chemical Formula 174] was synthesized by the following Scheme 35.

[Scheme 35]

[Formula 174]

[Chemical Formula 174] 3.9g (yield 49.2%) was obtained by synthesizing in the same manner except that <1-g> used in Scheme 12 was used instead of <9-e> synthesized in Scheme 33.

MS(MALDI-TOF): m/z 605.26[M] ⁺

Anal. Calc. for C ₄₂ H ₃₁ N ₅ C,83.28; H, 5.16; N, 11.56. Found C, 83.28; H, 5.15; N, 11.57

Example : Preparation of organic light emitting diode

The ITO glass was patterned so that the light emitting area was 2 mm × 2 mm in size and washed. After mounting the substrate in a vacuum chamber, the base pressure is 1 × 10 ^-6 torr, and then the organic material is placed on the ITO DNTPD (700 Å), NPD (300 Å), the compound prepared by the present invention + (piq) ₂ Films were formed in the order of Ir(acac) (10%) (300 Å), Alq ₃ (350 Å), LiF (5 Å), and Al (1,000 Å), and measured at 0.4 mA.

Comparative example

The organic light-emitting diode device for the comparative example was fabricated in the same manner, except that CBP, which is commonly used as a phosphorescent host material, was used instead of the compound prepared according to the invention in the device structure of the above example. .

<CBP>

division Host Dopant Doping concentration% V Cd/㎡ CIEx CIEy Comparative Example 1 CBP (piq) ₂ Ir(acac) 10 7.52 1000 0.671 0.328 Example 1 3 (piq) ₂ Ir(acac) 10 3.97 1611 0.673 0.327 Example 2 4 (piq) ₂ Ir(acac) 10 3.06 1562 0.671 0.328 Example 3 5 (piq) ₂ Ir(acac) 10 3.57 1594 0.672 0.327 Example 4 7 (piq) ₂ Ir(acac) 10 3.24 1579 0.670 0.329 Example 5 8 (piq) ₂ Ir(acac) 10 3.37 1678 0.672 0.326 Example 6 9 (piq) ₂ Ir(acac) 10 4.02 1478 0.671 0.327 Example 7 34 (piq) ₂ Ir(acac) 10 3.84 1542 0.673 0.327 Example 8 35 (piq) ₂ Ir(acac) 10 3.98 1524 0.671 0.326 Example 9 36 (piq) ₂ Ir(acac) 10 3.47 1631 0.671 0.326 Example 10 44 (piq) ₂ Ir(acac) 10 3.66 1597 0.672 0.325 Example 11 45 (piq) ₂ Ir(acac) 10 3.71 1538 0.673 0.326 Example 12 46 (piq) ₂ Ir(acac) 10 3.86 1473 0.672 0.326 Example 13 54 (piq) ₂ Ir(acac) 10 3.46 1582 0.672 0.325 Example 14 55 (piq) ₂ Ir(acac) 10 3.99 1486 0.673 0.325 Example 15 56 (piq) ₂ Ir(acac) 10 3.06 1543 0.672 0.326 Example 16 84 (piq) ₂ Ir(acac) 10 3.91 1527 0.673 0.326 Example 17 85 (piq) ₂ Ir(acac) 10 3.21 1671 0.671 0.327 Example 18 86 (piq) ₂ Ir(acac) 10 3.36 1472 0.672 0.326 Example 19 172 (piq) ₂ Ir(acac) 10 3.66 1549 0.672 0.327 Example 20 173 (piq) ₂ Ir(acac) 10 3.94 1574 0.673 0.327 Example 21 174 (piq) ₂ Ir(acac) 10 3.74 1592 0.673 0.326 Example 22 234 (piq) ₂ Ir(acac) 10 3.54 1608 0.673 0.326

In addition, compounds included in the scope of the present invention (e.g., a range of structures in which one structure selected from Formulas A-1 to A-3 and the other structure selected from Formulas B-1 to B-4 are bonded) Or even a combination thereof may cause problems in which some compounds do not have luminescence uniformity at high temperatures, whereas the compounds of Formulas 3 to 253 above can also ensure very excellent luminescence uniformity at high temperatures. , In that the uniformity of light emission does not decrease based on area and time even after applying an electric field for a long time (e.g., more than 100 hours), the compounds of formulas 3 to 253 have high temperature light emission uniformity and area and time It was confirmed that it showed a specific effect of ensuring uniformity of light emission based on.

In addition, even if it is a combination of compounds included in the scope of the present invention, it is impossible to develop a viscosity of 7 cP or more without using a separate thickener, and thus film formation by the solution coating method was mostly impossible. 4, 5, 7, 8, 9, 34, 35, 36, 44, 45, 46, 54, 55, 56, 84, 85, 86, 172, 173, 174, 234 one selected from or a mixture thereof In the case of use, it was confirmed that the viscosity of 7 cP or more could be expressed without using a separate thickening agent, and thus film formation by the solution coating method was possible.

Claims (12)

An organic electroluminescent compound having a structure in which one structure selected from the following [Formula A-1] to [Formula A-3] and the other structure selected from the following [Formula B-1] to [Formula B-2] are combined :
[Formula A-1]

[Formula A-2]

[Formula A-3]

[Formula B-1]

[Formula B-2]

[Chemical Formula A-1] to [Formula A-3] in bold and the bold in the [Formula B-1] to [Formula B-2] has a structure in which a contact and bonded portion,
Z'is selected from a single bond, CR ₃₁ R ₃₂ , NR ₃₃ , O, S and SiR ₃₄ R ₃₅ ,
Q is NR ₁₇ ,
R ₃₁ to R ₃₅ and R ₁₇ are each independently hydrogen, deuterium, a substituted or unsubstituted alkyl group having 1 to 10 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms, and a substituted or unsubstituted carbon number of 6 to 60 Is selected from an aryl group and a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms,
And X ₁ and X ₂ is CRR of the Formula B-1], [Chemical Formula B-2] X ₁ and X ₂ is CR, wherein each R is independently hydrogen, deuterium, alkyl group having 1 to 10 carbon atoms in the , An aryl group having 6 to 60 carbon atoms or a heteroaryl group having 2 to 60 carbon atoms,
Y is CR"R", O or S (n is an integer of 0 to 1), and the R" are each independently hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 60 carbon atoms, or 2 to carbon atoms It is a heteroaryl group of 60,
R'is each independently hydrogen, deuterium, an alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 60 carbon atoms, or a heteroaryl group having 2 to 60 carbon atoms (a is an integer of 3 to 6),
B is -(L) _m -R ₁ ,
L is a single bond or a divalent selected from a substituted or unsubstituted alkylene having 1 to 60 carbon atoms, a substituted or unsubstituted arylene having 6 to 50 carbon atoms, and a substituted or unsubstituted heteroarylene having 3 to 50 carbon atoms. Is a linking group, m is an integer of 0 to 1,
R ₁ is selected from the following [Structural Formula 11],
[Structural Formula 11]

In [Structural Formula 11],
Each X is independently selected from a deuterium atom, a halogen atom, a cyano group, an alkyl group having 1 to 60 carbon atoms, a cycloalkyl group having 3 to 60 carbon atoms, an aryl group having 6 to 60 carbon atoms, and a heteroaryl group having 2 to 60 carbon atoms,
m is an integer of 1 to 9, when m is 2 or more, a plurality of Xs are the same as or different from each other, and at least one of the Xs is bonded to the R ₁ position by a single bond. The method of claim 1,
The R ₃₁ to R ₃₅ , R ₁₇ and L are each independently a deuterium atom, a halogen atom, a cyano group, an alkyl group having 1 to 60 carbon atoms, a cycloalkyl group having 3 to 60 carbon atoms, an aryl group having 6 to 60 carbon atoms, and 2 to carbon atoms. An organic electroluminescent compound, characterized in that further substituted with one or more substituents selected from 60 heteroaryl groups. delete delete delete delete The method of claim 1,
The organic electroluminescent compound is an organic electroluminescent compound, characterized in that any one selected from the following [Formula 3] to [Formula 253]:

[Formula 3] [Formula 4] [Formula 5] [Formula 6]

[Formula 7] [Formula 8] [Formula 9] [Formula 10]

[Formula 11] [Formula 12] [Formula 13] [Formula 14]

[Formula 15] [Formula 16] [Formula 17] [Formula 18]

[Formula 19] [Formula 20] [Formula 21] [Formula 22]

[Formula 23] [Formula 24] [Formula 25] [Formula 26]

[Formula 27] [Formula 28] [Formula 30] [Formula 31]

[Formula 32] [Formula 33] [Formula 34] [Formula 35]

[Formula 36] [Formula 37] [Formula 38] [Formula 39]

[Formula 40] [Formula 41] [Formula 42] [Formula 43]

[Formula 44] [Formula 45] [Formula 46] [Formula 47]

[Formula 48] [Formula 49] [Formula 50] [Formula 51]

[Formula 52] [Formula 53] [Formula 54] [Formula 55]

[Chemical Formula 56] [Chemical Formula 57] [Chemical Formula 58] [Chemical Formula 59]

[Formula 60] [Formula 61] [Formula 62] [Formula 63]

[Formula 64] [Formula 65] [Formula 66] [Formula 67]

[Formula 68] [Formula 69] [Formula 70] [Formula 71]

[Chemical Formula 72] [Chemical Formula 73] [Chemical Formula 74] [Chemical Formula 75]

[Chemical Formula 76] [Chemical Formula 77] [Chemical Formula 78] [Chemical Formula 79]

[Formula 80] [Formula 81] [Formula 82] [Formula 83]

[Formula 84] [Formula 85] [Formula 86] [Formula 87]

[Formula 88] [Formula 89] [Formula 90] [Formula 91]

[Formula 92] [Formula 93] [Formula 94] [Formula 95]

[Chemical Formula 96] [Chemical Formula 97] [Chemical Formula 98] [Chemical Formula 99]

[Formula 100] [Formula 101] [Formula 102] [Formula 103]

[Formula 104] [Formula 105] [Formula 106] [Formula 107]

[Formula 108] [Formula 109] [Formula 110] [Formula 111]

[Formula 112] [Formula 113] [Formula 114] [Formula 115]

[Chemical Formula 116] [Chemical Formula 117] [Chemical Formula 118] [Chemical Formula 119]

[Chemical Formula 120] [Chemical Formula 121] [Chemical Formula 122] [Chemical Formula 123]

[Formula 124] [Formula 125] [Formula 126] [Formula 127]

[Formula 128] [Formula 129] [Formula 130] [Formula 131]

[Formula 132] [Formula 133] [Formula 134] [Formula 135]

[Formula 136] [Formula 137] [Formula 138] [Formula 139]

[Formula 140] [Formula 141] [Formula 142] [Formula 143]

[Formula 144] [Formula 145] [Formula 146] [Formula 147]

[Formula 148] [Formula 149] [Formula 150] [Formula 151]

[Formula 152] [Formula 153] [Formula 154] [Formula 155]

[Formula 156] [Formula 157] [Formula 158] [Formula 159]

[Formula 160] [Formula 161] [Formula 162] [Formula 163]

[Formula 164] [Formula 165] [Formula 166] [Formula 167]

[Formula 168] [Formula 169] [Formula 170] [Formula 171]

[Formula 172] [Formula 173] [Formula 174] [Formula 175]

[Formula 176] [Formula 177] [Formula 178] [Formula 179]

[Formula 180] [Formula 181] [Formula 182] [Formula 183]

[Formula 184] [Formula 185] [Formula 186] [Formula 187]

[Formula 188] [Formula 189] [Formula 190] [Formula 191]

[Formula 192] [Formula 193] [Formula 194] [Formula 195]

[Chemical Formula 196] [Chemical Formula 197] [Chemical Formula 198] [Chemical Formula 199]

[Formula 200] [Formula 201] [Formula 202] [Formula 203]

[Formula 204] [Formula 205] [Formula 206] [Formula 207]

[Formula 208] [Formula 209] [Formula 210] [Formula 211]

[Chemical Formula 212] [Chemical Formula 213] [Chemical Formula 214] [Chemical Formula 215]

[Formula 216] [Formula 217] [Formula 218] [Formula 219]

[Formula 220] [Formula 221] [Formula 222] [Formula 223]

[Formula 224] [Formula 225] [Formula 226] [Formula 227]

[Formula 228] [Formula 229] [Formula 230] [Formula 231]

[Formula 232] [Formula 233] [Formula 234] [Formula 235]

[Formula 236] [Formula 237] [Formula 238] [Formula 239]

[Formula 240] [Formula 241] [Formula 242] [Formula 243]

[Formula 244] [Formula 245] [Formula 246] [Formula 247]

[Formula 248] [Formula 249] [Formula 250] [Formula 251]

[Chemical Formula 252] [Chemical Formula 253] An organic thin film layer for an organic electroluminescent device comprising at least one or more organic electroluminescent compounds according to claim 1. The method of claim 8,
The organic thin film layer comprises the organic electroluminescent compound as a host and further comprises at least one dopant compound. A first electrode; A second electrode; And the organic thin film layer according to claim 8 interposed between the first electrode and the second electrode. The method of claim 10,
The organic electroluminescent device further includes at least one layer selected from the group consisting of a light emitting layer, a hole injection layer, a hole transport layer, a hole blocking layer, an electron transport layer, an electron injection layer, and an electron blocking layer between the first electrode and the second electrode, ,
An organic electroluminescent device, wherein one of the emission layer, the hole injection layer, the hole transport layer, the hole blocking layer, the electron transport layer, the electron injection layer and the electron blocking layer is the organic thin film layer according to claim 8. The method of claim 10,
The organic light-emitting device is an organic light-emitting device, characterized in that it emits white light by including at least one organic light-emitting layer emitting blue, red, or green light.